(±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-4,5-dihydro­furan-3-carbonitrile

J Suresh; R Vishnupriya; P Gunasekaran; S Perumal; P L Nilantha Lakshman

doi:10.1107/S1600536812018430

. 2012 Apr 28;68(Pt 5):o1576. doi: 10.1107/S1600536812018430

(±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-4,5-dihydrofuran-3-carbonitrile

J Suresh ^a, R Vishnupriya ^a, P Gunasekaran ^b, S Perumal ^b, P L Nilantha Lakshman ^c,^*

PMCID: PMC3344671 PMID: 22590433

Abstract

The furan ring in the title compound, C₂₆H₁₈N₂O₂, is twisted about the C(H)—C(H) bond. The molecular structure is stabilized by an intramolecular C—H⋯O interaction, which generates an S(6) ring motif. The presence of N—H⋯N hydrogen bonds leads to inversion dimers, which are stabilized in the crystal packing by C—H⋯O and C—H⋯π interactions, forming layers that stack along the a axis.

Related literature

For graph-set notation, see: Bernstein et al. (1995 ▶). For the importance of furan derivatives, see: Kappe et al. (1997 ▶); Sato et al. (1999 ▶); Smith et al. (2002 ▶). For additional conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₆H₁₈N₂O₂
M _r = 390.42
Monoclinic,
a = 12.4027 (5) Å
b = 8.3722 (4) Å
c = 19.7472 (8) Å
β = 107.570 (2)°
V = 1954.85 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.17 × 0.14 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.974
20260 measured reflections
4403 independent reflections
3021 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.117
S = 1.02
4403 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018430/tk5086sup1.cif

e-68-o1576-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018430/tk5086Isup2.hkl

e-68-o1576-Isup2.hkl^{(211.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018430/tk5086Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the N1,C31,C32,C37,C38 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O1	0.93	2.56	3.040 (2)	112
C56—H56⋯O2ⁱ	0.93	2.45	3.330 (2)	158
N1—H1⋯N2ⁱⁱ	0.86	2.20	3.037 (2)	163
C43—H43⋯Cg1ⁱⁱⁱ	0.93	2.96	3.410 (2)	112

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

JS thanks the UGC for the FIST support. JS and RV thank the management of Madura College for their encouragement and support. PG thanks the CSIR for Junior and Senior Research Fellowships. SP thanks the Department of Science and Technology, New Delhi, for funding the Indo-Spanish collaborative major research project (grant: DST/INT/SPAIN/09).

supplementary crystallographic information

Comment

Benzofurans have physiological, pharmacological and toxic properties, and there is continuing interest in their synthesis (Kappe et al., 1997). Various benzofuran derivatives have been investigated as estrogen receptor ligands, because selective estrogen receptor modulators such as ralixofene have emerged as potential therapeutics for the prevention and treatment of osteoporosis (Sato et al., 1999; Smith et al., 2002). In view of their high medicinal value, and in conjunction with our research interests, we were prompted to synthesize and report the X-ray structure determination of the title compound, (I).

In the title compound (Fig. 1), the five-membered furanyl ring adopts a twisted conformation as evident from the puckering parameters (Cremer & Pople, 1975): Q = 0.1429 (2) Å and φ = 126.0 (6)°. The five-(N2,/C38/C31/C32/C37) and six-membered (C32—C37) rings in the indole group are planar, with a dihedral angle of 0.95 (1)° between them. The dihedral angle between the phenyl rings (C42—C47 and C51—C56) is 31.56 (1)°. The molecular structure is stabilized by an intramolecular C—H···O interaction which generates an S(6) ring motif (Bernstein et al., 1995).

The presence of N—H···N hydrogen bonds leads to inversion dimers which are stabilised in the crystal packing by C—H···O and C—H···π interactions, Table 1, to form layers that stack along the a axis, Fig. 2.

Experimental

To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-phenylacrylonitrile (1.0 eq.) and phenacylpyridinium bromide (1.0 eq.) in water (10 ml) was added drop-wise triethylamine (0.25 eq.) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 0.5 h. Then the separated free-flowing solid was filtered and washed with methanol (3 ml) to afford the title compound as pale-yellow solids. The product was recrystallized from EtOH/EtOAc mixture (1:1 ratio v/v ml) to give pure compound, as pale-yellow crystals. M. pt: 521 K; Yield: 88%.